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特戊酰苯基亚胺作为用于定向C-H键官能化的苯腈替代物。

Pivalophenone imine as a benzonitrile surrogate for directed C-H bond functionalization.

作者信息

Xu Wengang, Yoshikai Naohiko

机构信息

Division of Chemistry and Biological Chemistry , School of Physical and Mathematical Sciences , Nanyang Technological University , Singapore 637371 , Singapore . Email:

出版信息

Chem Sci. 2017 Aug 1;8(8):5299-5304. doi: 10.1039/c7sc01732d. Epub 2017 May 30.

DOI:10.1039/c7sc01732d
PMID:28970910
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5607892/
Abstract

Pivalophenone N-H imine has been found to serve as a prominent substrate for directed C-H alkylation and arylation reactions with alkyl bromides and aryl chlorides, respectively, under cobalt-N-heterocyclic carbene (NHC) catalysis. Unlike the case of the parent pivalophenone imine, the increased steric bulk of the resulting -substituted pivalophenone imines allows them to undergo clean imine-to-nitrile conversion under peroxide photolysis or aerobic copper catalysis conditions. Overall, these two-step transformations offer convenient synthetic methods for -functionalized benzonitriles.

摘要

已发现新戊苯乙酮N-H亚胺在钴-氮杂环卡宾（NHC）催化下，分别作为与溴代烷和芳基氯进行定向C-H烷基化和芳基化反应的重要底物。与母体新戊苯乙酮亚胺的情况不同，所得α-取代新戊苯乙酮亚胺增加的空间位阻使其能够在过氧化物光解或有氧铜催化条件下实现亚胺到腈的完全转化。总体而言，这些两步转化为α-官能化苯甲腈提供了便捷的合成方法。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8dd2/5607892/794a2fe583a3/c7sc01732d-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8dd2/5607892/cddf0d000bed/c7sc01732d-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8dd2/5607892/44536803e975/c7sc01732d-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8dd2/5607892/55b95c2667a9/c7sc01732d-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8dd2/5607892/794a2fe583a3/c7sc01732d-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8dd2/5607892/cddf0d000bed/c7sc01732d-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8dd2/5607892/44536803e975/c7sc01732d-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8dd2/5607892/55b95c2667a9/c7sc01732d-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8dd2/5607892/794a2fe583a3/c7sc01732d-s4.jpg

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